Long-standing debates about the ethical significance of sadomasochism have been raised by two recent legal cases, Pay v. United Kingdom and Mosley v. News Group Newspapers Limited. The judgements in these cases rely on the unexplained assumption that a person’s participation in sadomasochistic activities can call into question their suitability for certain social or public roles. The article evaluates this assumption by referring to developments within feminist and general academic thinking about the normative nature of sadomasochism, focusing in particular on key issues such as whether sadomasochism is sexist or racist and whether participating in sadomasochistic activities reflects negatively on a person’s character. After working through the various theoretical models of sadomasochism as replication, simulation, game playing and context dependent, the article contends that this assumption lacks both a compelling theoretical basis and a practical rationale. Instead, this article argues that law should more fully recognize the critical distinctions that exist between the ethical significance of sadomasochistic activities and the ethical significance of the frameworks of power inequality and narratives of oppression that sadomasochistic activities explicitly invoke or implicitly negotiate.